Linopirdine

Linopirdine
Clinical data
ATC code	N06BX09 (WHO) ;
Identifiers
	IUPAC name 1-phenyl-3,3-bis(pyridin-4-ylmethyl)-1,3-dihydro-2H-indol-2-one;
CAS Number	105431-72-9 ;
PubChem CID	3932;
IUPHAR/BPS	2599;
ChemSpider	3795 ;
UNII	I5TB3NZ94T;
KEGG	D04741 ;
ChEMBL	ChEMBL319111 ;
CompTox Dashboard (EPA)	DTXSID6045163 ;
Chemical and physical data
Formula	C26H21N3O
Molar mass	391.465 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N(c1ccccc1C2(Cc3ccncc3)Cc4ccncc4)c5ccccc5;
	InChI InChI=1S/C26H21N3O/c30-25-26(18-20-10-14-27-15-11-20,19-21-12-16-28-17-13-21)23-8-4-5-9-24(23)29(25)22-6-2-1-3-7-22/h1-17H,18-19H2 ; Key:YEJCDKJIEMIWRQ-UHFFFAOYSA-N ;
	(what is this?) (verify)

Linopirdine is a putative cognition-enhancing drug with a novel mechanism of action. Linopirdine blocks the KCNQ2\3 heteromer M current with an IC50 of 2.4nM^[1] disinhibiting acetylcholine release, and increasing hippocampal CA3-schaffer collateral mediated glutamate release onto CA1 pyramidal neurons.^[2] In a murine model linopirdine is able to nearly completely reverse the senescence-related decline in cortical c-FOS, an effect which is blocked by atropine and MK-801, suggesting Linopirdine can compensate for the age related decline in acetylcholine release.^[3] Linopirdine also blocks homomeric KCNQ1 and KCNQ4 voltage gated potassium channels which contribute to vascular tone with substantially less selectivity than KCNQ2/3.^[1]

Synthesis

The synthesis starts with a standard scheme for preparing indoxyls. Thus, acylation of diphenylamine with oxalyl chloride leads to the amide.

References

^ ^a ^b Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9694925, please use {{cite journal}} with |pmid=9694925 instead.
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 22674722, please use {{cite journal}} with |pmid=22674722 instead.
^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11378256, please use {{cite journal}} with |pmid=11378256 instead.
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1080/00397919308011258, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1080/00397919308011258 instead.

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[pmid9694925-1] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9694925, please use {{cite journal}} with |pmid=9694925 instead.

[pmid22674722-2] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 22674722, please use {{cite journal}} with |pmid=22674722 instead.

[pmid11378256-3] Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 11378256, please use {{cite journal}} with |pmid=11378256 instead.

[4] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1080/00397919308011258, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1080/00397919308011258 instead.

[1]

[2]

[3]

[4]

Synthesis

See also

References